tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate

Base Information

• Chemical Name: tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate
• CAS No.: 483368-24-7
• Molecular Formula: C₂₅H₂₆F₃N₃O₃
• Molecular Weight: 473.495
• Mol file: 483368-24-7.mol

Synonyms:tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate

Chemical Property of tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate

There total 4 articles about tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid (481055-29-2) + (4S)-fluoro-L-prolinamide p-toluenesulfonate (1064078-39-2) → tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate (483368-24-7)

Guidance literature:

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid; (4S)-fluoro-L-prolinamide p-toluenesulfonate; With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 20 ℃; for 0.5h; Large scale reaction;

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 40 - 80 ℃; Mechanism; Large scale reaction;

DOI:10.1021/op900178d

Reference yield: 90.0%

C25H28F3N3O4 → tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate (483368-24-7)

Guidance literature:

With pyridine; Methanesulfonic anhydride; In ethyl acetate; at 50 ℃;

DOI:10.1021/op900178d

Reference yield: 65.0%

(2S,4S)-4-fluoropyrrolidine-2-carbonitrile; 4-methylbenzene-1-sulfonic acid (483366-11-6) → tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate (483368-24-7)

Guidance literature:

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid; With O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexaflurophosphate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 0.5h;

(2S,4S)-4-fluoropyrrolidine-2-carbonitrile; 4-methylbenzene-1-sulfonic acid; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 12h; Product distribution / selectivity;

upstream raw materials:

(2S,4S)-4-fluoropyrrolidine-2-carbonitrile; 4-methylbenzene-1-sulfonic acid

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid

(4S)-fluoro-L-prolinamide p-toluenesulfonate

Downstream raw materials:

denagliptin tosylate

Denagliptin hydrochloride